# US 5,708,170 A · Arthropodicidal carboxanilides

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- Number: US 5,708,170 A
- Document ID: US5708170A
- Status: Granted
- Kind: A
- Application number: 08/448,086
- Filed: 1995-05-23
- Granted: 1998-01-13
- Earliest claimed: 1990-12-21
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Gary David Annis; William Eldo Barnette; Stephen Frederick McCann; Keith Dumont Wing
- Web page: https://patentgrep.com/patent/US5708170A

## CPC

- C07D 253/10: Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
- A01N 47/38: containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- C07D 273/04: Six-membered rings
- C07D 285/16: Thiadiazines; Hydrogenated thiadiazines
- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

Arthropodicidal carboxanilides of Formula I or II: ##STR1## wherein: Q is selected from the group ##STR2## A, E, G, X, X.sup.1, Y, Z, Z.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and n are as defined in the text, arthropodicidal compositions containing said compounds and a method for using the compounds to control arthropods.

## Claims

### Claim 1

A compound of Formula I or II: ##STR117## wherein: Q is selected from the group ##STR118## A is H; E is selected from the group H and C.sub.1 -C.sub.3 alkyl; or
A and E can be taken together to form --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --O--, --S--, --S(O)--, --S(O).sub.2 --, --NR.sup.7 --, --OCH.sub.2 --, --SCH.sub.2 --, --N(R.sup.7)CH.sub.2 --, substituted --CH.sub.2 --, and substituted --CH.sub.2 CH.sub.2 -- the substituents independently selected from 1-2 halogen and 1-2 methyl;
G is selected from the group ##STR119## X is selected from the group O, S and N-X.sup.2 ; X.sup.1 is selected from the group Cl, Br, OR.sup.8, SR.sup.8 and NR.sup.8 R.sup.9 ;
X.sup.2 is selected from the group R.sup.8, OH, OR.sup.8, CN, SO.sub.2 R.sup.8, SO.sub.2 Ph, OC(O)NR.sup.9 R.sup.10, OC(O)OR.sup.8, NR.sup.9 R.sup.10 and phenyl optionally substituted with R.sup.11 ;
Y is selected from the group H; C.sub.1 -C.sub.6 alkyl; benzyl; C.sub.2 -C.sub.6 alkoxyalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkyl optionally substituted with halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, CN, NO.sub.2, S(O).sub.r R.sup.32, COR.sup.32, CO.sub.2 R.sup.32, phenyl optionally substituted with halogen, CN, C.sub.1 -C.sub.2 haloalkyl and C.sub.1 -C.sub.2 haloalkoxy; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 cyclohaloalkyl; C.sub.3 -C.sub.6 cycloalkylalkyl; CHO; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; C.sub.2 -C.sub.6 haloalkylcarbonyl; COR.sup.36 ; CO.sub.2 R.sup.36 ; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; phenylthio; R.sup.12 OC(O)N(R.sup.13)S-- and R.sup.14 (R.sup.15)NS--;
A.sup.1 is H;
A.sup.1 and Y can be taken together to form --(CH.sub.2).sub.t --;
Z is C or N;
Z.sup.1 is NR.sup.31 ;
R.sup.1 and R.sup.2 are independently selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, NR.sup.18 C(O)R.sup.17, OC(O)NHR.sup.17, NR.sup.18 C(O)NHR.sup.17, NR.sup.18 SO.sub.2 R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when m or n is 2, (R.sup.1).sub.2 can be taken together, or (R.sup.2).sub.2 can be taken together as --OCH.sub.2 O--, --OCF.sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --CF.sub.2 CF.sub.2 O or --OCF.sub.2 CF.sub.2 O-- to form a cyclic bridge; provided that when R.sup.1 or R.sup.2 is S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17 or OS(O).sub.2 R.sup.17 then R.sup.17 is other than H;
R.sup.3 is selected from the group H, J, N.sub.3, NO.sub.2, halogen, N(R.sup.22)R.sup.23, C(R.sup.34).dbd.N--O--R.sup.35, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 alkoxylalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, CO.sub.2 R.sup.17, OR.sup.19, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, C(S)NR.sup.17 R.sup.18, C(S)R.sup.17, C(S)SR.sup.17, CN, Si(R.sup.28) (R.sup.29)R.sup.27, SR.sup.27, S(O)R.sup.27, SO.sub.2 R.sup.27, --P(O) (OR.sup.27).sub.2, phenyl, phenyl substituted with (R.sup.16).sub.p, benzyl and benzyl substituted with 1 to 3 substituents independently selected from W; or R.sup.3 is C.sub.2 -C.sub.6 epoxyalkyl optionally substituted with a group selected from C.sub.1 -C.sub.3 alkyl, CN, C(O)R.sup.24, CO.sub.2 R.sup.24 and phenyl optionally substituted with W; or R.sup.3 is C.sub.1 -C.sub.6 alkyl substituted with a group selected from C(O)N(R.sup.25)R.sup.26, C(O)R.sup.25, SR.sup.27, S(O)R.sup.27, SO.sub.2 R.sup.27, SCN, CN, C.sub.1 -C.sub.2 haloalkoxy, Si(R.sup.28) (R.sup.29)R.sup.30, N(R.sup.22)R.sup.23, NO.sub.2, OC(O)R.sup.25, --P(O) (OR.sup.27).sub.2 and J;
J is selected from the group saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing 1-4 heteroatoms independently selected from the group consisting of 0-2 oxygen, 0-3 sulfur and 0-4 nitrogen, this substituents optionally containing one carbonyl and optionally substituted with one or more members selected from W;
R.sup.4 and R.sup.5 are independently selected from the group H, C.sub.1 -C.sub.4 alkyl, COR.sup.20 and C.sub.2 -C.sub.4 alkoxycarbonyl; or
R.sup.4 and R.sup.5 can be taken together to form .dbd.O or .dbd.S;
R.sup.6 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 haloalkoxycarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl C.sub.2 -C.sub.4 haloalkoxycarbonyl, COR.sup.36, CO.sub.2 R.sup.36, C.sub.2 -C.sub.5 alkylaminocarbonyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.4 -C.sub.7 alkylcycloalkyl, C.sub.4 -C.sub.7 haloalkylcycloalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl and SO.sub.2 Ph optionally substituted with Cl, Br or CH.sub.3 ;
R.sup.7 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, R.sup.17, CO.sub.2 R.sup.17, C(O)NR.sup.17 R.sup.21, C(S)NR.sup.17 R.sup.21, C(S)R.sup.17, C(S)OR.sup.17, --P(O)(OR.sup.17).sub.2, --P(S)(OR.sup.17).sub.2, P(O)(R.sup.17)OR.sup.17, P(O)(R.sup.17)SR.sup.21, and optionally substituted phenyl and benzyl wherein the substituent(s) are selected from F, Cl, Br, CH.sub.3, CF.sub.3 or OCF.sub.3 ; provided that when R.sup.7 is other than C(O)R.sup.17, C(O)NR.sup.17 R.sup.21 or C(S)NR.sup.17 R.sup.21 then R.sup.17 is other than H;
R.sup.8 is selected from the group C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.6 cycloalkyl; C.sub.1 -C.sub.3 alkyl substituted with OCH.sub.3, OCH.sub.2 CH.sub.3, NO.sub.2, CN, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SCH.sub.3 or SCH.sub.2 CH.sub.3 and benzyl optionally substituted with R.sup.11 ;
R.sup.9 is selected from the group H, C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxycarbonyl, and optionally substituted phenyl and pyridine wherein the substituent(s) are selected from R.sup.15 ; or
R.sup.8 and R.sup.9 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- each of which is optionally and independently substituted with 1 or 2 CH.sub.3 groups;
R.sup.10 is selected from the group H and C.sub.1 -C.sub.4 alkyl; or
R.sup.9 and R.sup.10 can be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- each of which is optionally and independently substituted with 1 or 2 CH.sub.3 groups;
R.sup.11 is selected from halogen, CN, C.sub.1 -C.sub.3 haloalkyl and C.sub.1 -C.sub.3 haloalkoxy;
R.sup.12 is C.sub.1 -C.sub.6 alkyl;
R.sup.13 is C.sub.1 -C.sub.4 alkyl;
R.sup.14 and R.sup.15 are independently C.sub.1 -C.sub.4 alkyl; or
R.sup.14 and R.sup.15 can be taken together as --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
R.sup.16 is selected from the group C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, NR.sup.18 C(O)R.sup.17, OC(O)NHR.sup.17, NR.sup.18 C(O)NHR.sup.17, NR.sup.18 SO.sub.2 R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when p is 2, (R.sup.16).sub.2 can be taken together as --OCH.sub.2 O--, --OCF.sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --CF.sub.2 CF.sub.2 O or --OCF.sub.2 CF.sub.2 O-- to form a cyclic bridge; provided that when R.sup.16 is S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17 or OS(O).sub.2 R.sup.17 then R.sup.17 is other than H;
R.sup.17 is selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, and optionally substituted phenyl and benzyl wherein the substituents are 1 to 3 substituents independently selected from W;
R.sup.18 is selected from the group H and C.sub.1 -C.sub.4 alkyl; or
R.sup.17 and R.sup.18, when attached to the same atom, can be taken together as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
R.sup.19 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl and C.sub.1 -C.sub.4 alkylsulfonyl;
R.sup.20 is C.sub.1 -C.sub.3 alkyl;
R.sup.21 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl and C.sub.2 -C.sub.4 alkynyl;
R.sup.22 is selected from the group H, C.sub.2 -C.sub.7 alkylcarbonyl, C.sub.2 -C.sub.7 alkoxycarbonyl, optionally substituted C.sub.1 -C.sub.4 alkyl, optionally substituted C.sub.2 -C.sub.4 alkenyl, and optionally substituted C.sub.2 -C.sub.4 alkynyl, the substituents selected from C.sub.1 -C.sub.2 alkoxy, CN, C(O)R.sup.30 and C(O).sub.2 R.sup.27 ;
R.sup.23 is selected from the group H, C.sub.1 -C.sub.3 alkyl, phenyl, phenyl substituted with W, benzyl and benzyl substituted with W;
R.sup.24 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl and C.sub.2 -C.sub.4 alkynyl;
R.sup.25 and R.sup.26 are independently selected from the group H and C.sub.1 -C.sub.2 alkyl;
R.sup.27 is selected from the group C.sub.1 -C.sub.3 alkyl, phenyl and phenyl substituted with W;
R.sup.28 is C.sub.1 -C.sub.3 alkyl;
R.sup.29 is C.sub.1 -C.sub.3 alkyl;
R.sup.30 is selected from the group H, C.sub.1 -C.sub.3 alkyl, phenyl and phenyl substituted with W;
R.sup.31 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkylcarbonyl or C.sub.2 -C.sub.4 alkoxycarbonyl;
R.sup.32 is selected from the group C.sub.1 -C.sub.3 alkyl;
R.sup.34 is selected from the group H, Cl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 thioalkyl and CN;
R.sup.35 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 alkylcarbonyl and C.sub.2 -C.sub.3 alkoxycarbonyl;
R.sup.36 is selected from the group phenyl and phenyl substituted with W;
W is selected from the group halogen, CN, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfonyl and C.sub.1 -C.sub.2 haloalkylsulfonyl;
m is 1 to 3;
n is 1 to 3;
p is 1 to 3;
r is 0, 1 or 2;
t is 2 or 3; and
u is 1 or 2.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein Q is selected from Q-5 and Q-6.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein Q is selected from Q-1, Q-2, Q-3, and Q-4.

### Claim 4 (depends on 1)

A compound according to claim 1 wherein Q=Q.sub.1.

### Claim 5 (depends on 2, 3, 4)

A compound according to claim 2, 3 or 4 wherein J is selected from the group: ##STR120##

### Claim 6 (depends on 2, 3, 4)

A compound according to claim 2, 3 or 4 wherein:
R.sup.1 is selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, SCN, NO.sub.2, OR.sup.17, SR.sup.17, SO.sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; with one R.sup.1 substituent in the 4-position, or when m is 2 then (R.sup.1).sub.2 can be taken together as --CH.sub.2 C(CH.sub.3).sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --OCF.sub.2 CF.sub.2 O--, or --CF.sub.2 CF.sub.2 O-- to form a 5- or 6-membered fused ring;
R.sup.2 is selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W;
R.sup.3 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkoxycarbonylalkyl, CO.sub.2 R.sup.17, C(O)R.sup.17, phenyl and phenyl substituted by (R.sup.16).sub.p ;
R.sup.16 is selected from the group C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl,, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W;
R.sup.17 is selected from the group C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.4 alkenyl and propargyl;
R.sup.18 is selected from the group H and CH.sub.3 ;
X.sup.1 is selected from the group Cl, OR.sup.8, SR.sup.8 and N(CH.sub.3).sub.2 ;
X.sup.2 is selected from the group R.sup.8, OR.sup.8 and N(CH.sub.3).sub.2 ;
m is 1 or 2;
n is 1 or 2; and
p is 1 or 2.

### Claim 7 (depends on 4)

A compound according to claim 4 wherein G is selected from the group G-2, G-1, G-6 and G-9.

### Claim 8 (depends on 4)

A compound according to claim 4 wherein A and E are taken together to form --O--, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --S--, --SCH.sub.2 -- or NR.sup.7 ; R.sup.7 is selected from the group H, Me, SO.sub.2 R.sup.17, CO.sub.2 R.sup.17 and CON(R.sup.17)R.sup.21.

### Claim 9 (depends on 1, 2, 3, 4, 7, 8)

An arthropodicidal composition comprising a compound according to any one of claims 1, 7, 8, 2, 3 or 4 and a carrier therefor.

### Claim 10 (depends on 1, 2, 3, 4, 7, 8)

A method for controlling arthropods comprising contacting them or their environment with an arthropodicidally effective amount of a compound according to any one of claims 1, 7, 8, 2, 3 or 4.